A person with a diamond head.
Correct. An arrow pointing upwards from a pillar, offset slightly to the right.
Correct! A downward pointing arrow with a wrench head.
No, not that one. This shape has a big arrow pointing down.
No, not that one. This is a big arrow pointing downwards with a grabber head at the bottom.
No, not that one. Let's try a different shape: a long chair with a bent back.
Correct, but remove the previous shape, it is wrong.
No, that's the opposite of what I said. Put the chair back and remove the toothpaste tube.
REMOVE THE TOOTHPASTE TUBE
Correct. Now add the tall, vertical shape.

Outcome: unsuccessful
Speaker comments: Bot flip-flopped between listening well and being very obstinate.